Preston Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

32 Houses

20

Maryland’s Eastern Shore Welcomes You

Maryland / Preston

Preston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 50 mi
  • Swimming pool
  • Child Friendly

Price per night from

$100

Price per night from

$100

23

EASTERN SHORE MARYLAND WELCOMES YOU

Maryland / Preston

Preston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$87

Price per night from

$87

Great rentals within 20 miles that match your search

Distance approx 13.33 km from Preston

29

NEW! Colonial Home in Cambridge w/Wraparound Porch

Maryland / Cambridge

Cambridge house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$264

Responds fast!
avg. 10 minutes

Price per night from

$264

Distance approx 11.29 km from Preston

(1) Very Good 

34

Waterfront Room Rentals 1 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$149

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$149

Distance approx 11.28 km from Preston

(5) Average 

55

Waterfront Vacation Home with Private Beach

Talbot County / Trappe

Trappe house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Child Friendly

Price per night from

$380

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$380

Distance approx 13.05 km from Preston

16

Choptank River View House

Maryland / Cambridge

Cambridge house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Price per night from

$1,149

Price per night from

$1,149

Distance approx 17.67 km from Preston

(4) Excellent 

Certificate of Excellence

129

Sun and Sand Loft- just minutes to the beach:) Hot tub

Delaware / Greenwood

Greenwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Certificate of Excellence

Price per night from

$63

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$63

Distance approx 11.29 km from Preston

42

Waterfront Room Rentals 2 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$115

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$115

Distance approx 18.87 km from Preston

13

Luxury Apartment with Private Entrance

Maryland / Centreville

Centreville apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$135

Price per night from

$135

Distance approx 14.59 km from Preston

4

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Talbot County / Royal Oak

Royal Oak house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$686

Price per night from

$686

Distance approx 17.67 km from Preston

(7) Very Good 

Certificate of Excellence

151

TAKE a BUBBLE BATH in the WOODS! Your BARN RETREAT- 2BR,BEACH 17M JACUZZI/PETS

Delaware / Greenwood

Greenwood barn

2 16 1 night min

  • 2 bedrooms
  • sleeps 16
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$91

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$91

Distance approx 11.29 km from Preston

44

Waterfront Room Rentals 3 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$115

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$115

Distance approx 17.62 km from Preston

(11) Very Good 

30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Talbot County / St. Michaels

St. Michaels house

7 9 min stay varies

  • 7 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
…see more

Price per night from

$332

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$332

Distance approx 17.66 km from Preston

(24) Excellent 

27

Location Location! St Michaels-- In Town Cottage!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$172

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$172

Distance approx 14.51 km from Preston

8

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Maryland / Cambridge

Cambridge house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$996

Price per night from

$996

Distance approx 17.84 km from Preston

(2) Excellent 

139

ROMANTIC PRIVATE APARTMENT GETAWAY- 17 Miles to BEACHES & BAY--Pets!!

Delaware / Farmington

Farmington apartment

1 12 1 night min

  • 1 bedroom
  • sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 17 mi
  • Child Friendly

Price per night from

$91

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$91

Distance approx 17.66 km from Preston

(13) Excellent 

24

Premier Cottage in St. Michaels- In Town Location!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$173

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$173

Distance approx 17.21 km from Preston

(2) Excellent 

18

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

Talbot County / St. Michaels

St. Michaels house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$263

Price per night from

$263

Distance approx 15.11 km from Preston

18

Historic Waterfront Property with Wi-Fi and Dock

Talbot County / St. Michaels

St. Michaels house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$859

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$859

Distance approx 17.68 km from Preston

(7) Very Good 

23

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

Distance approx 17.64 km from Preston

(3) Very Good 

25

Waterview Cottage In St. Michaels!

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

Distance approx 12.13 km from Preston

15

Tranquil Easton Waterfront Property

Talbot County / Easton

Easton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$690

Price per night from

$690

Distance approx 18.19 km from Preston

15

Lakeside Private Apartment

Talbot County / Wye Mills

Wye Mills apartment

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$160

Price per night from

$160

Distance approx 18.46 km from Preston

(3) Excellent 

Certificate of Excellence

138

2 BR PRIVATE NATURE RETREAT- BEACHES 17 M- JACUZZI, OUTDOOR SHOWER

Delaware / Rehoboth Beach

Rehoboth Beach apartment

2 10 1 night min

  • 2 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Certificate of Excellence

Price per night from

$91

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$91

Distance approx 19.87 km from Preston

12

Harris Cove Cottages LLC

Talbot County / St. Michaels

St. Michaels cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 18.62 km from Preston

14

Halo's Haven Guest Quarters

Talbot County / St. Michaels

St. Michaels house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$374

Price per night from

$374

Distance approx 17.4 km from Preston

7

St. Michael's Premier in Town Summer Cottage!

Talbot County / St. Michaels

St. Michaels house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$327

Price per night from

$327

Distance approx 18.5 km from Preston

(4) Very Good 

Certificate of Excellence

142

Nature Retreat- Awesome Studio Apartment- Just Minutes to Beach:) 2 Beds, H.Tub

Delaware / Rehoboth Beach

Rehoboth Beach room

1 8 1 night min

  • 1 bedroom
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 29 mi
  • Child Friendly

Certificate of Excellence

Price per night from

$45

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$45

Distance approx 17.95 km from Preston

(1) Average 

38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

Talbot County / St. Michaels

St. Michaels villa

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Price per night from

$1,145

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$1,145

Distance approx 14.63 km from Preston

(10) Excellent 

24

RESTORED WATERFRONT COTTAGE

Talbot County / Royal Oak

Royal Oak cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$344

Price per night from

$344

Distance approx 19.64 km from Preston

(15) Excellent 

35

Year Round Estate on Bay / Fam. Reunions / Slps 28

Maryland / Cambridge

Cambridge house

7 28 min stay varies

  • 7 bedrooms
  • sleeps 28
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop
…see more

Price per night from

$1,000

Price per night from

$1,000

Distance approx 17.39 km from Preston

(10) Excellent 

50

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Maryland / Cambridge

Cambridge cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$169

Price per night from

$169